Date: Thu, 19 Feb 2009 23:37:03 -0800 (PST)
From: RE
Subject: "In Over My Head" part 2

Walking in any new school is frightening enough under normal circumstances,
but it is even worse when you are a guy pretending to be a girl. Since I
was a new student, I had to stop at a table outside the counselors office
and pick up my schedule and information packet.

"Oh, you must be Kylie!" the counselor exclaimed, introducing herself. I
smiled and said, "Hi," wandering if my voice was convincing. I had
practiced this enough, even mimicking girls on TV.

"If you have any difficulty finding your way around, you be sure and stop
by our office," she continued. Here, let me get somebody to show you where
your first class is at. She glanced around the hallway, then loudly said,
"Joel, can you come here?" A guy with brown hair and glasses looked up from
his locker, then came over. He was of medium build, and looked more the
studious type than the athlete.

"Joel, this is Kylie. She just moved here from California. Do you mind
showing her where the Math department is at for her first period class? Are
you headed that way?"

Joel glanced over, sizing me up quickly. "Sure, no problem. I'm going that
way," he said, and I noticed the North Carolina accent. He had a soft,
almost shy voice. "C'mon, I can help you get your locker, too, if you
haven't found it yet."

"Thanks," I murmured, once again worrying about my voice. The more I used
it, the easier it became.

Within minutes, I was chatting with Joel, and he became my unofficial tour
guide as he showed me down the hallway. I noticed students look up at me,
and when we passed some jocks standing outside the cafeteria, I felt like
they were sizing me up. I stole a glance back as we went by, and one tall
guy was staring at my back side- he saw me look back, and grinned
sheepishly, then turned away. Maybe I was just being self conscious.

When I got to my locker, Joel offer to help me with the combination and the
handle, which was sticking. He had bought into my charade as a female with
no question, and I genuinely liked him so far.

"Now your class is down on the left," he directed me with his hand, "and I
have the same lunch as you do, so I'll check in and make sure everything is
ok. You'll find that this is a big school, but everyone is pretty
friendly. Southern hospitality!"

After my first three classes, I found my way to the lunchroom. Several
students had chatted with me and asked about California. No one questioned
my sexuality, so I assumed I was comfortable in my new role. Once I almost
messed up by going to the boy's restroom. After that, I tried to avoid
bathrooms altogether. I decided that I wouldn't go during passing periods-
only at times that no one was around. My PE class wasn't until second
semester, so I didn't have to worry about that. I figured I would get a
schedule change before then, and avoid it altogether.

Joel was waiting at the door when I went into the cafeteria and, after
getting some food, we sat down. He introduced me to a few friends-male and
female, and then everyone held the usual kind of conversation. Apparently
there was a back-to- school dance later that week that some of them were
headed to. Rachel and Brenna invited me to go with them and, since they had
a car, we made plans for them to pick me up. Joel was undecided, since
school dances weren't really his interest, but he said he might show up
just to see everybody.

The rest of the week went reasonably well, and since my mother didn't come
in until late in the evenings, I didn't have to worry about changing
outfits until after I returned home. I began to wander what I should wear
to the dance, but it was pretty informal so I figured a pair of jeans would
probably work. When Rachel pulled up to the curb, I was watching for her
and jumped in the back seat. I was relieved to see that she had dressed
about the same as I had. We had both put on a little more jewelry and
cosmetics than what we normally wore at school. I had also made sure to
shave what little hair might have existed on my legs and underarms. My face
was already smooth.

The Dance

When we walked in the school gym, a few students looked up, but most of
them were pre-occupied, so we got a Coke and went to stand in the side of
the dance floor to watch the students who were brave enough to get in front
of their classmates. Before long the numbers increased, the lights went
down, the volume went up, and everybody relaxed. A couple of times I saw a
guy looking over my way that looked like a junior or senior. He had curly,
dark hair and dark features- taller than me, but not too big. We made eye
contact, and he looked down bashfully, then looked back up and smiled. I
smiled back, then continued talking to Brenna, watching him out of the
corner of my eye. I knew he was watching me, even while he chatted with
some other guys.

My heart pounded as he broke away from the other guys and started moving my
way. He was adorable- bright white teeth below a tanned face, with a shy,
nervous look. His black curly hair was natural, and really hot.. He was
dressed in jeans and a collared shirt over an olive green t-shirt. I
realized that he may be coming over to see one of the other girls, but I
felt my face grow warm.

"Hey, Brenna, who's your friend?" he smiled.

"Oh, hey," she said looking up. "This is Kylie. She just moved in here."

He looked at me and said, "Welcome, welcome. I'm glad ta meet ya!" with a
big smile. "I'm Drew- I was Andy in elementary school, but I decided Drew
sounded smarter, so I changed my name. Do you want to dance?"

"Yeah, I guess so," I replied sheepishly, "but I'm not that good." I was
nearly terrified- I was a guy, parading as a girl, about to dance with a
guy who would probably spit on me if he knew the truth, but he was really
hot, and I loved the southern accent.

"I'm glad you're not good, 'cause now I won't feel so bad if I step on your
feet," he said, reaching out for my hand.

We moved out on the floor which was playing a slower song now, and it was
obvious that neither of us were very good dancers (which I think helped us
relax a bit.) We talked a little bit about California, and he told me that
he ran cross country and track, but avoided football and other sports
because of the time it took, and that he had a job that kept him busy in an
electronics store. I never noticed what a guy smelled like, until now. When
you're a guy, you don't notice guy smells but, when you're parading as a
perfumed girl, you pick up on this. It smelled good. I was glad I had a
girdle strapped around holding my hard-on at bay, especially when he
nuzzled up next to my cheek.

The rest of the night, we stayed pretty close to each other between songs,
and made a few more lame attempts on the dance floor. No one else seem to
notice, or to care.  As things started winding down, he asked if he could
take me home. I told Rachel, and she just gave a thumbs up and said, "you
behave yourself, you hear? He might not be as sweet and innocent as you
think!"

Parking for the First Time

We left in his small pickup truck, which didn't have a lot of seat space,
so when his hand dropped from the gear shifter to my leg, I knew he was
testing me for a response. I reached down and covered his hand with mine,
and pressed it into my leg. "Don't let him move into my crotch, I begged
myself- he might feel it, and then I'm in big trouble."

Fortunately he didn't make any moves in that direction, but he asked if I
wanted to drive around the reservoir which was the cities water supply. It
was still early, so I wasn't too worried about the time.

"I want to show you a really cool view up near the damn," he said, glancing
over, "if you're ok with it."

"Sure," I answered, "I'm ok with it." I hoped he would read between the
lines.

When we stopped at the small parking area near the damn, it was completely
deserted. There was a small nightlight not far that shined weakly on his
truck. He said, "Here it is, what do you think?"

It wasn't that impressive, but I said, "Yeah, this is really cool. I'm glad
we drove over here."

He turned to face me, then lifted the hand from my leg to my chin and
pulled it toward him and kissed me lightly on the lips. I pressed in, and
he kissed me more aggressively, and I felt the flicker of his tongue. I
couldn't believe this was happening- I was literally floating on air, as I
kissed back.  I had kissed a few girls, and a time or two I had played
around with some guys in San Francisco that were buddies staying overnight
with me in middle school, but that wasn't really kissing- not like
this. This was the real thing, and the more I gave in, the more aggressive
he became, sliding his tongue further in my mouth.

"Mmm, you taste sooo good," he murmured in my ear, giving it a small lick,
then moving back to my mouth. "Are you ok with this?" he whispered, as his
hand ran down my back, "you have me so hot for you...."

Fearing exposure if he touched my breasts, I pushed back a little and
said,"whew, I better catch my breath!"

Getting the message, he backed off a little and said, "sorry, you just
really get me going. I've been watching you all week, since class started."
He reached down and took my hand and placed it on his knee. "You are so
beautiful...."

I reached up and took his face and kissed him again, then slid down to his
neck and found a soft spot to gently suck on. I felt some light beard
stubble, and could taste some of the cologne he was wearing.

"Oh....,"he said, as he put his hand on the back of my head, "I like
that....but what I'd really like to do is to fuck you....d'you want to do
it? if not, I understand....," he almost begged.

Whoa- kissing was a HUGE step, but fucking? I mean, I can't even do THAT! I
had to think really fast..

"Oh, uh, I want to so much but....um, I'm having my period right now....I
can't do it....but you know I want to...." I could see the disappointment
in his eyes.

"Oh, Kylie, you got me going so bad.....wow....you are so hot," he
moaned. "Would you give me head? I know some girls don't do it 'cause they
think its gross and all, but I keep really clean."

Blow jobs I knew a little- be it, very little- about, because of messing
around in 8th grade with some buddies, even if they could barely shoot a
load. I reached down, and rubbed his jeans, and felt the hardness
underneath, then found the zipper and snap.

"Are you really going to?" he whimpered, fumbling with his pants, and
trying to help me pull them down. "Oh, this is so sweet, so very hot.....,"
he groaned as his cut, 6" boner broke free, and he slid his undershorts
down. I could smell fresh fabric softener and a little musky odor of
sweat. I held it is my hand, and glanced up at his face..

"If this is your first time, just lick it like a popsicle or a sucker, it
don't taste bad," he instructed. "That sticky stuff on the end is ok, it
won't hurt anything." Boy, he must have thought this was the first cock
that I ever saw! And I had one of my own that was about to burst. I held it
up and licked the head, tasting the pre-cum that was really flowing
heavily. It didn't have a lot of taste, but it was pretty slimy. After
playing with the head and licking up and down the shaft a few times, I
swallowed the whole thing.

It was electrifying! He jumped and grabbed my head and said, "Ewww! Oh,
that's wild, that's wild!" I reached under his balls with my other hand and
pulled on them. One thing that a guy knows, is what a guy would like in a
blow job. I gently tugged on his balls while I moved up and down the shaft
and he squirmed and moaned.

I knew an instant before that it was about to happen- he tensed and tried
to push my head off of his rod, and then the fountain of juice started
shooting. I was just at the head when it started, and it went down my
throat, in my mouth, and then caught my lips and even my face. Jism was
going everywhere all at once. I didn't hesitate to swallow what was in my
mouth, then go back for more. He must have shot for two or three minutes
before he finally leaned back and dropped his arms to the side, his dick
still in my mouth.

As he rubbed my hair, he said, "I am sooo sorry- I wasn't going to shoot in
your mouth like that....I didn't mean too. I was trying to push you off
when it happened. I hope it didn't make you sick."

I laid my head in his lap, and looked up at his embarrassed, anguished
look. Then I pulled his face down and kissed him gently, but enough to
smear the goo between us.

By now his cock was a soft pile of skin, and I let him pull up his own
pants since he obviously felt uncomfortable.

Our ride back was quiet, but he did reach over and take my hand. I didn't
know if tonight was a one time experience, or if he would ask me again.
Maybe he just wanted me to get his rocks off and nothing else. I guess I
would have to see.